SBA Crosslinker | CAS# 42014-51-7 | Crosslinker

MedKoo Cat#: 571607 | Name: SBA Crosslinker

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

SBA crosslinker, or N-Succinimidyl bromoacetate, is a sulfhydryl (thiol) and amino reactive heterobifunctional protein crosslinking reagent. SBA protein crosslinker is non-cleavable and is among the shortest amine and sulfhydryl reactive crosslinking reagents known with a spacer arm length of only 1.5 Angstroms. SBA Crosslinker is useful for making antibody drug conjugates (ADCs).

Chemical Structure

SBA Crosslinker

CAS#42014-51-7

Theoretical Analysis

MedKoo Cat#: 571607

Name: SBA Crosslinker

CAS#: 42014-51-7

Chemical Formula: C6H6BrNO4

Exact Mass: 234.9480

Molecular Weight: 236.02

Elemental Analysis: C, 30.53; H, 2.56; Br, 33.85; N, 5.93; O, 27.11

Price and Availability

Size	Price	Availability
1g	USD 250.00	2 Weeks
5g	USD 650.00	2 Weeks
10g	USD 950.00	2 Weeks

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Synonym

Bromoacetic acid N-hydroxysuccinimide ester; Succinimidyl bromoacetate; SIB crosslinker; NHS-Bromoacetate; N-Succinimidyl bromoacetate

IUPAC/Chemical Name

N-Succinimidyl bromoacetate

InChi Key

NKUZQMZWTZAPSN-UHFFFAOYSA-N

InChi Code

InChI=1S/C6H6BrNO4/c7-3-6(11)12-8-4(9)1-2-5(8)10/h1-3H2

SMILES Code

O=C(ON1C(CCC1=O)=O)CBr

Appearance

Purity

>97% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

SBA crosslinker is a heterobifunctional protein crosslinking reagent.

In vitro activity:

Peptides derived from human fibrin were linked to three carrier proteins (bovine serum albumin, bovine alpha-lactalbumin, and keyhole limpet hemocyanin) using SBA crosslinker. SBA crosslinker allowed conjugation by first modifying carrier proteins with bromoacetate and then linking them to cysteine-containing peptides. S-carboxymethylcysteine was liberated, indicating successful linkage between peptide and protein. The efficiency of peptide incorporation ranged from 22% to 37%. Reference: Anal Biochem. 1986 May 15;155(1):95-102. https://pubmed.ncbi.nlm.nih.gov/3717562/

In vivo activity:

To be determined

	Solvent	mg/mL	mM
Solubility
	Acetone	25.0	105.92

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 236.02 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Bernatowicz MS, Matsueda GR. Preparation of peptide-protein immunogens using N-succinimidyl bromoacetate as a heterobifunctional crosslinking reagent. Anal Biochem. 1986 May 15;155(1):95-102. doi: 10.1016/0003-2697(86)90231-9. PMID: 3717562. 2. Davies ME, Knight CG, Mativi BY. Antibodies to a short synthetic peptide cross-react with human recombinant interleukin 1 alpha. Immunol Lett. 1988 Dec;19(4):293-7. doi: 10.1016/0165-2478(88)90158-7. PMID: 3266612.

In vitro protocol:

In vivo protocol:

To be determined

1: Zhao HM, Ma L, Lin D, Han KK, Chun Y, Xu QH. Preparation of cross-linked bimodal mesoporous SBA-15 with numerous pore openings. J Nanosci Nanotechnol. 2012 Dec;12(12):8955-62. PubMed PMID: 23447944. 2: Bhange P, Sridevi N, Bhange DS, Prabhune A, Ramaswamy V. Immobilization of bile salt hydrolase enzyme on mesoporous SBA-15 for co-precipitation of cholesterol. Int J Biol Macromol. 2014 Feb;63:218-24. doi: 10.1016/j.ijbiomac.2013.11.008. Epub 2013 Nov 25. PubMed PMID: 24286937. 3: Vinoba M, Bhagiyalakshmi M, Jeong SK, Yoon YI, Nam SC. Immobilization of carbonic anhydrase on spherical SBA-15 for hydration and sequestration of CO2. Colloids Surf B Biointerfaces. 2012 Feb 1;90:91-6. doi: 10.1016/j.colsurfb.2011.10.001. Epub 2011 Oct 6. PubMed PMID: 22024402. 4: Endo M, Tipper JL, Barton DC, Stone MH, Ingham E, Fisher J. Comparison of wear, wear debris and functional biological activity of moderately crosslinked and non-crosslinked polyethylenes in hip prostheses. Proc Inst Mech Eng H. 2002;216(2):111-22. PubMed PMID: 12022418. 5: Gao S, Wang Y, Diao X, Luo G, Dai Y. Effect of pore diameter and cross-linking method on the immobilization efficiency of Candida rugosa lipase in SBA-15. Bioresour Technol. 2010 Jun;101(11):3830-7. doi: 10.1016/j.biortech.2010.01.023. Epub 2010 Feb 8. PubMed PMID: 20116998. 6: Kim BC, Lee J, Um W, Kim J, Joo J, Lee JH, Kwak JH, Kim JH, Lee C, Lee H, Addleman RS, Hyeon T, Gu MB, Kim J. Magnetic mesoporous materials for removal of environmental wastes. J Hazard Mater. 2011 Sep 15;192(3):1140-7. doi: 10.1016/j.jhazmat.2011.06.022. Epub 2011 Jun 17. PubMed PMID: 21752538. 7: Zholobenko VL, Khodakov AY, Impéror-Clerc M, Durand D, Grillo I. Initial stages of SBA-15 synthesis: an overview. Adv Colloid Interface Sci. 2008 Oct 1;142(1-2):67-74. doi: 10.1016/j.cis.2008.05.003. Epub 2008 Jun 4. PubMed PMID: 18599009. 8: Baxter RM, MacDonald DW, Kurtz SM, Steinbeck MJ. Characteristics of highly cross-linked polyethylene wear debris in vivo. J Biomed Mater Res B Appl Biomater. 2013 Apr;101(3):467-75. doi: 10.1002/jbm.b.32902. Epub 2013 Feb 22. PubMed PMID: 23436587; PubMed Central PMCID: PMC3928672. 9: Godula K, Bertozzi CR. Density variant glycan microarray for evaluating cross-linking of mucin-like glycoconjugates by lectins. J Am Chem Soc. 2012 Sep 26;134(38):15732-42. Epub 2012 Sep 12. PubMed PMID: 22967056; PubMed Central PMCID: PMC3458438. 10: Fernández-Fernández M, Sanromán MÁ, Moldes D. Recent developments and applications of immobilized laccase. Biotechnol Adv. 2013 Dec;31(8):1808-25. doi: 10.1016/j.biotechadv.2012.02.013. Epub 2012 Feb 28. Review. PubMed PMID: 22398306. 11: Gupta D, Bhattacharyya L, Fant J, Macaluso F, Sabesan S, Brewer CF. Observation of unique cross-linked lattices between multiantennary carbohydrates and soybean lectin. Presence of pseudo-2-fold axes of symmetry in complex type carbohydrates. Biochemistry. 1994 Jun 21;33(24):7495-504. PubMed PMID: 8031418. 12: Dam TK, Gerken TA, Brewer CF. Thermodynamics of multivalent carbohydrate-lectin cross-linking interactions: importance of entropy in the bind and jump mechanism. Biochemistry. 2009 May 12;48(18):3822-7. doi: 10.1021/bi9002919. PubMed PMID: 19292456; PubMed Central PMCID: PMC2691598. 13: Qiang Z, Guo Y, Liu H, Cheng SZ, Cakmak M, Cavicchi KA, Vogt BD. Large-scale roll-to-roll fabrication of ordered mesoporous materials using resol-assisted cooperative assembly. ACS Appl Mater Interfaces. 2015 Feb 25;7(7):4306-10. doi: 10.1021/am5086275. Epub 2015 Feb 10. PubMed PMID: 25635350. 14: Lee J, Kim J, Kim J, Jia H, Kim MI, Kwak JH, Jin S, Dohnalkova A, Park HG, Chang HN, Wang P, Grate JW, Hyeon T. Simple synthesis of hierarchically ordered mesocellular mesoporous silica materials hosting crosslinked enzyme aggregates. Small. 2005 Jul;1(7):744-53. PubMed PMID: 17193518. 15: Dessen A, Gupta D, Sabesan S, Brewer CF, Sacchettini JC. X-ray crystal structure of the soybean agglutinin cross-linked with a biantennary analog of the blood group I carbohydrate antigen. Biochemistry. 1995 Apr 18;34(15):4933-42. PubMed PMID: 7711015. 16: Khan MI, Mandal DK, Brewer CF. Interactions of concanavalin A with glycoproteins. A quantitative precipitation study of concanavalin A with the soybean agglutinin. Carbohydr Res. 1991 Jun 25;213:69-77. PubMed PMID: 1933954. 17: Gupta D, Bhattacharyya L, Fant J, Macaluso F, Sabesan S, Brewer CF. Observation of unique cross-linked lattices between multiantennary carbohydrates and soybean lectin. Presence of pseudo-2-fold axes of symmetry in complex type carbohydrates. Biochemistry. 1994 May 10;33(18):5614-22. Corrected and republished in: Biochemistry. 1994 Jun 21;33(24):7495-504. PubMed PMID: 8180186. 18: Mencucci R, Marini M, Gheri G, Vichi D, Sarchielli E, Bonaccini L, Ambrosini S, Zappoli Thyrion GD, Paladini I, Vannelli GB, Sgambati E. Lectin binding in normal, keratoconus and cross-linked human corneas. Acta Histochem. 2011 May;113(3):308-16. doi: 10.1016/j.acthis.2009.12.003. Epub 2010 Jan 6. PubMed PMID: 20053427. 19: Olsen LR, Dessen A, Gupta D, Sabesan S, Sacchettini JC, Brewer CF. X-ray crystallographic studies of unique cross-linked lattices between four isomeric biantennary oligosaccharides and soybean agglutinin. Biochemistry. 1997 Dec 9;36(49):15073-80. PubMed PMID: 9398234. 20: Brewer CF. Lectin cross-linking interactions with multivalent carbohydrates. Adv Exp Med Biol. 2001;491:17-25. PubMed PMID: 14533787.